Woodside

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Maybe more than any other affluent Peninsula community, Woodside loves its past; so much so that it keeps reminders of its humble beginnings all around town.

Woodside doesn't have the perfumed roots of an Atherton or a Hillsborough. It began life as a rough-and-tumble logging town. By 1855 it had eight sawmills and one shingle mill. Whiskey Hill Road got its name from the abundance of saloons that once called it home. It wasn't until the 1880s that wealthy San Franciscans caught wind of Woodside and began building their weekend estates there. Once they came, they stayed.

Today, Woodside enjoys a reputation as one of the most affluent communities in the United States. It's held onto its rural roots, though; Woodside attracts tycoons who enjoy the land and the outdoors. On weekends, its streets fill up with road cyclists and equestrians, so many that it's normal to see bicycles and horses tied up outside Roberts Market, Woodside's unofficial town meeting place. There are three equestrian organizations in Woodside, including the Woodside-area Horse Owners Association; that's right: WHOA.

Unlike Atherton and Hillsborough, Woodside does allow businesses within its city limits. It doesn't have a traditional compact downtown, though. Instead, businesses – and locals – congregate along Woodside Road, between Whiskey Hill and Canada Road. That's where you'll find Roberts Market, some shops and a few restaurants, notably Buck's, an eatery whose down home atmosphere belies the legendary number of million- and billion-dollar tech deals said to have gone down there. According to restaurant owner Jamis MacNiven, only one Silicon Valley bigwig never ate at Buck's: Woodside resident Steve Jobs, who'd many years before hired MacNiven as a contractor and been unsatisfied with the results.

Other famous Woodside residents, past and present, include Michelle Pfeiffer, Charles Schwab, John Baez, Carl Degrassi, Intel Corporation founder Gordon Moore, former U.S. Representative Pete McCloskey and Larry Ellison, whose nine-year efforts to build a $200 million, Japanese-inspired Woodside home is something of a local legend.

A few hundred feet from Buck's is Woodside Town Hall, along with a pair of relics from the town's early days, Independence Hall and the Pioneer Saloon, the latter being last remaining nightspot on Whiskey Hill Road. Further down the road is the Woodside Store, a preserved relic from the town's early days. Nearby Filoli Mansion, a holdover from the days of the great country estates, is now a museum and arts center.

Woodside is a town of barely 5,000 occupants, but its city limits stretch all the way into the Santa Cruz Mountains. You can live in Woodside and be conveniently close to Highway 280 or you can live in Woodside and be surrounded by Redwoods, far from your nearest neighbor. The town includes two of San Mateo County's largest public parks, Huddart Park and Wunderlich County Park, enormous open spaces with miles of hiking trails and fields.

What sets this town apart from other affluent areas, though, is its sense of community. Woodside locals don't hide in their homes; they ride horses and bicycles, attend the annual Kings Mountain Art Fair, join WHOA and linger over breakfast at Buck's. They come out in droves for the annual Woodside School Auction, enjoying a dazzling evening out and raising breathtaking sums for Woodside's only public school.

Woodside has seemingly done the impossible, earning a slot on Forbes' and Businessweek's "Wealthiest American Towns" list while hanging onto its rustic, relaxed roots. Among affluent Bay Area communities, it stands alone.